Open AccessRecent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene
Author(s) -
Rebecca Boutin,
Samuel Koh,
William Tam
Publication year - 2019
Publication title -
current organic synthesis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.292
H-Index - 46
eISSN - 1875-6271
pISSN - 1570-1794
DOI - 10.2174/1570179416666181122094643
Subject(s) - chemistry , nucleophile , stereocenter , reactivity (psychology) , catalysis , cyclopropane , allylic rearrangement , regioselectivity , palladium , combinatorial chemistry , rhodium , alkene , transition metal , ligand (biochemistry) , ring (chemistry) , cyclopropanation , iridium , organic chemistry , enantioselective synthesis , medicine , biochemistry , alternative medicine , receptor , pathology
Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active.